Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 24, 2024
Abstract
Studies
on
the
transformations
of
some
functionalized
cycloalkene
derivatives
through
their
ring
olefin-bond
aziridination/aziridine
opening
with
fluoride
are
presented.
The
selected
model
compounds
submitted
to
fluorinative
functionalization
were
an
amino
ester
and
diesters
a
cyclohexene
skeleton
as
well
cyclopentene-fused
β-lactam.
Functionalization
proceeded
across
substrate-directed
diastereoselective
aziridination,
followed
by
fluoride-mediated
aziridine
or
intramolecular
lactonization
giving
fluorinated
lactone
derivatives.
Catalysis Science & Technology,
Journal Year:
2024,
Volume and Issue:
14(18), P. 5143 - 5160
Published: Jan. 1, 2024
This
review
article
summarizes
the
visible
light
mediated
synthesis
of
allenes
from
substrates
like
1,3-enynes,
propargylic
carbonates,
homopropargylic
alcohols,
oxalates,
alkynyl
diazo
compounds,
and
terminal
aziridines.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(16), P. 12310 - 12317
Published: Aug. 2, 2024
Aziridines
are
important
targets
for
synthetic
chemistry,
and
many
methods
involving
the
aziridination
of
alkenes
by
olefins
with
nitrenes
have
been
reported.
In
general,
however,
nitrene
transfer
reactions
optimized
a
limited
range
precursors,
synthesis
structurally
diverse
aziridines
featuring
N-substituents
requires
application
multiple
varying
reaction
conditions.
Herein,
we
report
photocatalytic
method
that
operates
wide
N-substituted
precursors.
A
combination
synthetic,
spectroscopic,
computational
data
is
consistent
mechanism
generation
triplet
intermediates.
The
effectiveness
4DPAIPN
as
photocatalyst
this
process
can
be
rationalized
consequence
its
exceptionally
long
lifetime,
rather
than
excited
state
energies
or
redox
properties
in
isolation.
Chemistry - An Asian Journal,
Journal Year:
2024,
Volume and Issue:
19(22)
Published: Aug. 13, 2024
Abstract
2,5‐disubstituted
N
,
N’
‐alkylpiperazines
represent
an
interesting
target
in
organic
synthesis
both
for
pharmaceutical
or
agrochemical
applications
and
as
a
promising
class
of
ligands
coordination
chemistry.
We
report
here
microwave‐enhanced
these
compounds
starting
from
non‐activated
N‐
alkyl
aziridines
the
presence
catalytic
amounts
simple
ammonium
metallates.
A
remarkable
TOF
2787.9
h
−1
has
been
observed
case
[TBA]
2
[ZnI
4
]
catalyst
(catalyst
loading
0.1
mol
%)
with
almost
complete
selectivity
(up
to
97
favor
diastereoisomers
(
meso
chiral
form)
piperazines,
obtained
1
:
ratio.
The
two
isomers
are
easily
separated,
because
form
precipitates
pure
reaction
crude.
stereochemical
investigation
unprecedented
isolation
2,6‐disubstituted
allowed
us
shed
light
on
mechanism.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(11)
Published: Aug. 24, 2023
Abstract
The
aziridination
of
chalcones
with
iminoiodinanes
under
photoredox
conditions
has
been
reported.
reaction
proceeds
through
nitrene
radical
anion
intermediate
generated
from
iminoiodinanes.
trapping
anions
by
afforded
trans
‐aziridine
products
exclusively.
scope
the
in
terms
both
substrates
is
considerably
wide
and
most
cases
‐3‐aryl‐aziridine‐2‐ketones
were
isolated
good
yields.
challenging
due
to
electron‐deficient
nature
substrate,
making
this
only
second
example
(after
trifluoromethyl
alkenes)
photocatalytic
double
bonds.
Polymer Chemistry,
Journal Year:
2023,
Volume and Issue:
14(45), P. 5034 - 5039
Published: Jan. 1, 2023
Orthogonal
polymerization
of
aziridine
and
cyclic
carbonates
is
developed
for
constructing
amphiphilic
block
copolymers,
followed
by
acidification
to
construct
polysomes.
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
19(2)
Published: Nov. 29, 2023
Abstract
An
in
situ
generated
photoactive
copper(I)‐complex‐catalyzed
aziridination
reaction
of
cyclic
N‐sulfonyl
imines
with
α‐aryl‐substituted
vinyl
azides
irradiated
by
blue‐LEDs
light
is
reported
for
the
first
time.
This
novel
SET
process
represents
a
mild,
sustainable,
and
pragmatic
method
accessing
synthetically
resourceful
sulfamidate‐fused
aziridines
acceptable
chemical
yields
excellent
diastereoselectivities.
Delightedly,
pharmacologically
attractive
benzo[
f
][1,2,3]oxathiazepine
dioxides
fused
isoxazoline
frameworks
were
achieved
through
our
newly
developed
metal‐free
based
ring‐expansion
techniques,
highlighting
synthetic
value
accessed
aziridines.
Finally,
possible
mechanism
[2+1]
aza‐cyclization
was
presented
on
conduction
series
control
experiments.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(13), P. 2554 - 2557
Published: Jan. 1, 2024
A
cobalt-catalyzed
ring
opening,
nucleophilic
amination
of
aziridines
and
azetidines
with
N
-fluorosulfonamides
has
been
established
toward
a
wide
range
1,2-
1,3-diamine
derivatives
in
moderate
to
good
yields
under
mild
conditions.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 8656 - 8667
Published: June 4, 2024
The
nucleophilic
ring-opening
of
aziridine
derivatives
provides
an
important
synthetic
tool
for
the
preparation
various
β-functionalized
amines.
Amines
as
nucleophiles
are
employed
to
prepare
synthetically
useful
1,2-diamines
in
presence
catalysts
or
activators.
Herein,
B2(OH)4-mediated
reductive
transformation
N-tosyl
aziridines
by
nitroarenes
was
developed.
This
aqueous
protocol
cheap
and
readily
available
amino
sources
proceeds
under
external
catalyst-free
conditions.
Control
experiments
DFT
calculations
pointed
situ
reduction
aryl
amines
via
N-aryl
boramidic
acid
(E)
SN1-type
N-tosylaziridines
resultant
with
high
regioselectivity.
